p-Toluenesulfonic acid → Ethyl (3,4,6-Trifluoro-2-methylbenzoyl)acetate

HRID 2271271

Reaction equation

HRID 2271271 reaction equation
[CH3:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[C:3]=1[C:4]([CH:6](C(OCC)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[CH:18]=[C:17]([F:23])[C:3]=1[C:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 17879412Diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate

Product 1

HCID 14517129Ethyl (3,4,6-Trifluoro-2-methylbenzoyl)acetateYield 82.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5.1 g of diethyl 2-methyl-3,4,6-trifluorobenzoylmalonate were added 20 ml of water and 30 mg of p-toluenesulfonic acid, followed by heating and refluxing for 2.5 hours. After cooling, the mixture was extracted with diethyl ether. The extract was dried over magnesium sulfate and concentrated to give 3.3 g of ethyl 2-methyl-3,4,6-trifluorobenzoylacetate.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 2.5 hours
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with diethyl ether
  5. dry with materialThe extract was dried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-991ad80c1386408da891fc79a06e5c96
Source dataset
uspto-grants-2001_12
Patent number
US06333431B1

Linked notes

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